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Chitose derivates using octreotide as target ligand and use thereof in medicament

A technology of chitosan derivatives and drugs, applied in the field of polymer chemistry, to achieve the effect of reducing toxic side effects and improving delivery efficiency

Inactive Publication Date: 2011-06-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research report on the modification of polymer materials and nanocarriers such as micelles and liposomes with octreotide

Method used

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  • Chitose derivates using octreotide as target ligand and use thereof in medicament
  • Chitose derivates using octreotide as target ligand and use thereof in medicament
  • Chitose derivates using octreotide as target ligand and use thereof in medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Preparation of N-octyl chitosan (NOC)

[0038] Add 3.5 g of chitosan, 105 mL of water, and 2.2 mL of acetic acid to a 500 mL three-necked flask, and stir for 2 hours. 105 mL of anhydrous methanol and 1 mL of acetic anhydride were added to the three-necked flask, and the reaction was incubated for 6 h, and the pH of the reaction solution was adjusted to 7 with 1 molL of NaOH. Add 10.6mL octanal, react at room temperature for 36h, slowly add 5g KBH 4 , the reaction solution was reduced at room temperature for 24h, the pH of the reaction solution was adjusted to 7, filtered, washed twice with water, 4 times with methanol, 2 times with ether, and dried to obtain 4.0g of yellow powder (octyl substitution degree 65%).

[0039] 2. Preparation of N-octyl-N-succinyl chitosan (NONSC)

[0040] Take 1 g of N-octyl chitosan, suspend it in 50 mL of dimethyl sulfoxide, stir for 1 h, add 0.56 g of succinic anhydride, stir vigorously at 80 °C for 24 h, adjust the pH of the reaction...

Embodiment 2

[0048] 1. Preparation of N-nonylchitosan (NNC)

[0049] Use chitosan to react with acetic anhydride and nonanal, and use KBH 4 Reduction, that is, the preparation method is the same as the preparation of NOC in Example 1.

[0050] 2. Preparation of N-nonyl-N-succinyl chitosan (NNNSC)

[0051] It is prepared by reacting N-nonyl chitosan with succinic anhydride, and the preparation method is the same as the preparation of NONSC in Example 1.

[0052] 3. Preparation of Octreotide Grafted N-Nonyl-N-Succinyl Chitosan (NNNSOC)

[0053] It is prepared by reacting N-nonyl-N-succinyl chitosan with octreotide, and the preparation method is the same as the preparation of NONSOC in Example 1.

[0054] NNNSOC:

[0055] FT-IR: 3428, 2951, 2871, 1728, 1669, 1656, 1551, 1426, 1381, 1315, 1258, 1231, 1151, 1116, 1071, 1036, 868cm -1 .

[0056] 1 H NMR (500MHz, D 2 O): 7.5-6.9 (arom Phe), 4.6-4.5 (Hα Thr, Hα Lys, H 1 ), 4.2(HβThr), 4.1-4.0(HβThr-ol), 4.0-3.4(Hβ 3 , H 4 , H 5 , H 6 ...

Embodiment 3

[0059] 1. Preparation of N-dodecyl chitosan (NLC)

[0060] Use chitosan to react with acetic anhydride and lauraldehyde, and use KBH 4 Reduction, that is, the preparation method is the same as the preparation of NOC in Example 1.

[0061] 2. Preparation of N-dodecyl-N-succinyl chitosan (NLNSC)

[0062] It is prepared by reacting N-dodecyl chitosan with succinic anhydride, and the preparation method is the same as the preparation of NONSC in Example 1.

[0063] 3. Preparation of Octreotide Grafted N-Dodecyl-N-Succinyl Chitosan (NLNSOC)

[0064] It is prepared by reacting N-dodecyl-N-succinyl chitosan with octreotide, and the preparation method is the same as the preparation of NONSOC in Example 1.

[0065] NLNSOC:

[0066] FT-IR: 3423, 2956, 2863, 1729, 1668, 1656, 1549, 1420, 1381, 1316, 1259, 1236, 1158, 1112, 1066, 1033, 869cm -1 .

[0067] 1 H NMR (500MHz, D 2 O): 7.5-6.9 (arom Phe), 4.6-4.5 (Hα Thr, Hα Lys, H 1 ), 4.2 (Hβ Thr), 4.1-4.0 (Hβ Thr-ol), 4.0-3.3 (H 3 ,...

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Abstract

The invention relates to the field of polymer chemistry and the field of pharmaceutical excipients. The invention particularly relates to targeted chitosan derivatives (I) or (II) containing octreotide, in particular to the N-succinyl-N-alkylate chitosan derivative and the N-alkylate carboxymethyl chitosan and a preparation method thereof, the invention further relates to an effect thereof as a solubilizer of an insoluble drug, a modification effect on micelles, liposomes and other vectors and a pharmaceutical composition which leads the derivatives to have the target function and contains the derivatives.

Description

technical field [0001] The invention relates to the field of polymer chemistry and the field of pharmaceutical excipients. Specifically, it relates to targeted chitosan derivatives containing octreotide, especially N-succinylated N-alkylated chitosan derivatives and N-alkylated carboxymethyl chitosan derivatives capable of forming amphiphilic polymer molecules Polysaccharide and its preparation method, the present invention also relates to its function as a poorly soluble drug solubilizer, its modification effect on carriers such as micelles and liposomes, so that it has a targeting function and a pharmaceutical composition containing it. Background technique [0002] Nanotechnology and biodegradable polymer materials are hot areas of current drug delivery system research. Polymeric micelles combine the advantages of both, which can be biodegradable and form drug nanocarriers. As a drug carrier, it can provide a series of unparalleled advantages: solubilize poorly soluble d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K9/00A61K9/127A61K38/12A61K31/337A61K31/4745A61K31/704C08B37/08A61P35/00A61K9/107A61K47/36
Inventor 平其能张灿张鹏申慰王宇
Owner CHINA PHARM UNIV
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